Sulfydryl modified high-molecular compound, and preparation method and application thereof

A polymer compound and modification technology, which is applied in the field of mercapto-modified polymer compounds and their preparation, can solve problems such as low solubility, inability to produce large-scale industrial production, and difficulty in industrial operation

Pending Publication Date: 2021-05-18
블라파르바이오테크놀로지항저우리미티드
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Specifically, the method overcomes the following shortcomings and deficiencies in the prior art: 1) The modification reagent needs to be synthesized through multi-step reactions, such as: dithiodihydrazide method and modified dithiodihydrazide method; 2) In the synthesis process of the modification reagent, highly toxic organic substances such as hydrazine hydrate need to be used, which does not meet the development needs of green chemistry or an environment-friendly society; 3) The thiol modification method involving the EDCI coupling agent needs to maintain the pH of the reaction system during the activation stage = 4.75, after entering the gel stage, it is impossible to achieve a stable and uniform reaction system through homogenization such as stirring, and the industrial operation is difficult; 4) The synthesis of HA-SH by the Ethylene sulfide method needs to be carried out unde

Method used

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  • Sulfydryl modified high-molecular compound, and preparation method and application thereof
  • Sulfydryl modified high-molecular compound, and preparation method and application thereof
  • Sulfydryl modified high-molecular compound, and preparation method and application thereof

Examples

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Example Embodiment

[0198][Method for preparing mercapto-modified polymer compound]

[0199]As previously mentioned, the present invention provides a method of preparing the above thiol-modified polymer compound, comprising the steps of:

[0200]1) Structure contains -COOH, -NH2, The acryloyation step of the polymer compound in -OH, is -COOH, -NH in the structure of the polymer compound.2At least one of -OH is directly or indirectly connected to the following group:

[0201]

[0202]R1R2R3The definition is the same; * indicates the connection point;

[0203]Alternatively, the acrylate group shown in the formula A is structured, and the acrylamide group shown in the above formula B, the polymer compound in the acryloyl group shown in the above formula C is directly used as a reaction raw material;

[0204]2) At least one of the polymer compound obtained by step 1) and a multi-proliferative compound HS-R4-Sh reaction, r4The definition is prepared to prepare the mercapto-modified polymer compound.

[0205]In a specific embodi...

Example Embodiment

[0228]Preparation Example 1 Synthetic acrylate modified hyaluronic acid (referred to as HA-A1)

[0229]Add 1 gram of penetrated acid (purchased from Huaxi Freda) in 200 ml beaker, with a weight average molecular weight of about 300kDa), 50 ml deionized water, 50 ml dimethylformamide, 12 ml of triethylamine, 14 ml of acrylic glycerides. After stirring at room temperature, stirring was continued for 48 hours. 300 ml of acetone was added to produce a large amount of white precipitation. The precipitate obtained by centrifugation was dissolved in 100 ml of deionized water to give a colorless transparent solution. The above solution is loaded into the dialysis bag (excluding molecular weight 8 kDa), and 5 liter of ion water is used for 5 days, and water is converted twice daily. Finally, the dialysis bag was collected, and 921 mg of white flocculated solid was obtained after freeze-drying, i.e., HA-A1, yield of 92.1%.

[0230]HA-A1 structureFigure 37 .Figure 37 It is only a schematic diagram, ...

Example Embodiment

[0232]Preparation Example 2 Synthetic acrylate modified hyaluronic acid (referred to as HA-A2)

[0233]1 gram of 1 gram of penetrated acid (purchased from Huaxi Freda) in 200 ml beaker, with a weight average molecular weight of approximately 400kDa), 50 ml of deionized water, 50 ml of dimethylformamide, 6.3 g methacrylic anhydride, stir Dissolve. The solution pH = 8 ± 0.5 per liter of NaOH was maintained, and stirring was continued for 24 hours. 300 ml of acetone was added to produce a large amount of white precipitation. The precipitate obtained by centrifugation was dissolved in 100 ml of deionized water to give a colorless transparent solution. The above solution is loaded into the dialysis bag (intercepted molecular weight 8kda, Shi must pure), 5 liter ion water dialysis for 5 days, and converted twice daily. Finally, the dialysis bag was collected, and 789 mg of white flocculated solid was obtained after freeze-drying, i.e., HA-A2, yield of 78.9%.

[0234]HA-A2 structureFigure 38 .

[0...

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Abstract

The invention relates to a sulfydryl modified high-molecular compound, and a preparation method and application thereof. The sulfydryl modified high-molecular compound is prepared from an acryloyl derivative modified high-molecular compound and a multi-sulfydryl compound through a Michael addition reaction of mercaptan and conjugated double bonds. The preparation method not only can realize the structure target of the sulfydryl modified high-molecular compound disclosed by the invention, but also has the following advantages: the structure and composition of the synthetic product, the variety and content of a large number of compound molecular functional groups and the like can be flexibly and effectively controlled; a reagent with high biocompatibility is adopted, so that the production cost is effectively controlled, and the toxicity in the synthesis process is reduced; and under the condition that a safe reagent and simple reaction steps are adopted, the obtained sulfydryl modified biocompatible polymer series compound which can be used as an extracellular matrix material and has good raw material structure and biological activity and adjustable functional group type and content according to needs can be obtained, and various clinical application requirements are met.

Description

technical field [0001] The invention belongs to the field of polymer materials, and in particular relates to a mercapto-modified polymer compound and its preparation method and application. Background technique [0002] Biocompatible polymers have many important physiological functions. Common biocompatible polymers include: polysaccharides, proteins, and synthetic polymers. Among them, the typical natural biocompatible polymer is hyaluronic acid. In 1934, Professor Karl Mayer extracted natural hyaluronic acid from the vitreous body of the bull's eye for the first time. Natural hyaluronic acid is composed of D-glucuronic acid and N-acetyl A natural heteropolysaccharide composed of alternating units of D-glucosamine. After decades of research, it was found that it widely exists in the connective tissues of humans and other vertebrates, such as intercellular spaces, sports joint tissues, umbilical cords, skin, cartilage, blood vessel walls, synovial fluid, and cockscombs and ...

Claims

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Application Information

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IPC IPC(8): C08B37/08C08G65/334C08H1/00C08F20/20C08F16/06C08F8/34
CPCC08B37/0072C08B37/0069C08B37/003C08H1/00C08G65/3344C08F8/34C08F20/20C08F16/06C08L89/06C08F122/1006C08L71/02C08G65/3342C08L5/08C08B37/0063C08G65/334C08F20/38
Inventor 王文新
Owner 블라파르바이오테크놀로지항저우리미티드
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